Tope Awotona's Unwavering Determination

How He Built Calendly Into a $3B company

Hey there my friend, Justin here, and welcome to Just Go Grind, a newsletter for the ambitious. Thank you to the 128 of you who joined since the last edition, if you aren't subscribed, and want to join 850 other subscribers, please subscribe below:

Take a look at the first two profiles, of Sam Altman of OpenAI and Melanie Perkins of Canva, as well as all of my other writing here!

Together with Masterworks

Billionaires wanted it, but 54,578 everyday investors got it first… and profited

When incredibly rare and valuable assets come up for sale, it's typically the wealthiest people that end up taking home an amazing investment. But not always

One platform is taking on the billionaires at their own game, buying up and fractionalizing some of history’s most prized blue-chip artworks for its investors.

It's called Masterworks. Their nearly $1 billion collection includes works by greats like Banksy, Picasso, and Basquiat, all of which are collectively owned by everyday investors. When Masterworks sells a painting – like the 16 it's already sold – investors reap their portion of the profits.

Offerings can sell out in minutes, but Just Go Grind readers can skip the waitlist to join with this exclusive link.

The story of Tope Awotona is one of impatience, persistence, and a ridiculous level of self-belief.

Tope is the Founder and CEO of Calendly, the scheduling software company last valued at $3B and used by more than 10 million users at 50,000 companies worldwide.

His journey, including starting multiple companies along the way, flying to another country to find tech talent, and overcoming doubters, serves as inspiration for those who want to build a business on their terms.

Let’s get to it.

Early Days

Tope was born in 1981 in Lagos, Nigeria, and was the third of four children.

His dad was a microbiologist and his mom was a pharmacist.

At a young age, it was clear Tope was special, and he was able to skip a couple of grades in middle school as part of a program for the gifted kids in his school. He’d actually end up graduating high school in Lagos at age 15 because of this.

But he also experienced tragedy early in life.

When he was only 12 years old, Tope saw his father shot and killed in a carjacking.

A few years later, in 1996, he’d move to Atlanta, where he actually went back to high school because his mother thought he was too young to go right to college.

When asked if he wanted to go to college at age 15, here’s what Tope said:

Absolutely I wanted to go. I’ve always been crazy impatient since I was a kid. In my mind, I was thinking I could be done with college sooner, and you know, start a business, do whatever, start my career earlier.

Tope Awotona

That crazy impatience would certainly help him later on in his career.

In deciding where he’d go to college, he ended up choosing the University of Georgia, but something he said about this decision stood out to me:

I thought about going to Stanford, but I didn’t think I could afford it. The cost of travel, the tuition was ten times higher than Georgia, I’m away from family. I just didn’t think I could afford it. Which I was right.

Tope Awotona

He thought about going to Stanford, but couldn’t afford it.

How many other talented kids are in this same position?

Working at VITALIZE Venture Captial and seeing how the VC industry works, it’s easy to see why talented people like Tope fall through the cracks, just because they didn’t attend top schools or come from certain companies.

Not every founder fits that Sam Altman profile of a Stanford dropout after all.

Just a reminder that unicorn founders can come from anywhere.

I digress.

But back to Tope’s story.

Tope’s First Business Attempt

Working at CVS during his freshman year of college, Tope had the idea to create a smarter cash register:

I worked in the photo lab, but inevitably what would happen was at the end of every night, the manager on duty would have to reconcile the cash register: count the money, look at what the computer says, review the total number of transactions each register did and make sure there was the same amount of money in the registers that there should be.

That process is like an hour for the manager every single night and I thought to myself wait a minute, what if you had a register, where instead of having the register open to the cashier, what if you had some machine where the customer actually feeds money into the machine, so the money never passes the hand into the cashier and therefore they never touch the money. This would prevent what managers called “leaking” and reduce the opportunities for cashiers to steal or make mathematical mistakes and also create a quicker closing process at the end of the night.

So that was my idea, to retrofit existing registers in this manner.

Tope Awotona

Tope would even go so far as to find a patent lawyer, file a provisional patent for his idea, and call NCR (National Cash Register).

When they were surprised by his age, being only a 17-year-old at the time, he was discouraged and didn’t end up pursuing it further.

This would be the first in a series of businesses with a reoccurring theme - note the right founder-market fit.

In other words, not the right business for Tope.

That self-awareness he had at the time is actually remarkable for a 17-year-old though and only continues to grow from there, with Tope switching majors from computer science to business management:

Sitting behind a computer and debugging this code didn’t completely engage me. So I started having second thoughts thinking, “Yes I can do this, but is this really what I want to do with my life.” And then fast forward in the summer, I took a job selling alarm systems door-to-door for ADT.

Tope Awotona

He CAN do it, but is that what he really wants to do?

So important and a nugget of wisdom lost on many people.

So Tope decides to get into sales, which, as you’ll soon find out, will lead him to start Calendly.

The Seeds of Calendly

After graduating college, Tope takes a sales job at a travel agency, selling luxury travel experiences.

He’s making good money and traveling the world, but a few years in he wants something different, so he lands a role at IBM doing software sales in 2006.

His work ethic is clear:

I always had the top call volume—I forget the number specifically—I also picked up the phone a lot faster than most other people did. I also learned and understood the different operating systems. The product we sold was really technical. We were selling backup storage software, so most people had a tough time getting comfortable with it.

Tope Awotona

But he wanted to be an account executive and he knew it would take way too long for him to rise up the ranks at IBM. There’s that impatience I mentioned previously.

And although he knows he still wants to be an entrepreneur, he doesn’t think he’s ready yet.

So he leaves IBM and joins a company, Perceptive Software, to which he’d attribute much of Calendly’s success.

Why was Perceptive Software so important to Tope starting Calendly?

  1. He worked with the “best and brightest” from different fields

  2. It was a fun but difficult environment

  3. The company was fast-growing and aligned with his ambitions

  4. The founder gave a talk about starting the company and how you can make it if you have enough perseverance

Tope’s experience at Perceptive Software showed him something I also discovered from doing 400+ podcast interviews - successful founders are human too.

As Tope would say about the experience:

It opened my eyes that people who start great companies are very human and very ordinary in most ways. What is extraordinary about them is they take action. They see something and they grab it rather than wait for someone else to come fix it. And then of course, there is a lot of uncertainty along the way and they learn fast and they adjust and they just figure it out. That was an aha moment for me. That was the first time where I was like, you know what, entrepreneurship is attainable for me. These people are smart and I think I’m just as smart as they are and I can do it as well.

Tope Awotona

After about two and a half years working at Perceptive Software in Kansas City, Tope moves back to Atlanta to work at Vertafore.

Now he’s got some money, is more confident in his skills, and he’s again ready to try to start a business.

Enter ProjectorSpot.

Business #2 - ProjectorSpot

It’s 2010, Tope is an account manager at Vertafore, and he actually decides he wants to buy a business.

While searching for a business to buy, he ends up talking to someone who convinces him to start a business in e-commerce, selling projectors.

But it doesn’t go as planned.

In an Atlanta Ventures interview, he breaks it down:

What I realized quickly, was that people who wanted to buy projectors wanted to be educated. People were going to to learn about projectors before they buy. I realized, for me to get good at that, I needed now to create educational content and I needed to learn about all different projectors. Long story short, I realized for me to get good at that, I needed to learn a lot more about projectors, and said to myself, this is not going to be a passive thing. It’s going to take work to grow this and it’s going to take a long time to grow this and, by the way, the margins suck because you’re selling someone else’s stuff.

Tope Awotona

It reminds me of the first sentence in Paul Graham’s phenomenal essay on doing what you love, “To do something well you have to like it.”

Tope didn’t like projectors.

At least not enough to spend a considerable amount of his time trying to build a business around them.

ProjectorSpot lasts less than 6 months before Tope shuts it down.

He’s still working full-time though and this gives him the capital to fund his next business - YardSteals.

Business #3 - YardSteals

At this point, it’s sometime around 2012, and, learning from his first e-commerce business experience, Tope decides to start another.

YardSteals, as he would later describe, is slightly better than ProjectorSpot.

He decides to go after selling home and garden yard equipment online. These have larger margins and seem like a better opportunity.

But the same problem arises.

People are looking to be educated around what are the best products to buy and Tope isn’t passionate about the products he’s selling.

This business also only lasts a few months, but Tope finally realizes he needs to pick a problem to solve that already exists and that he’s passionate about.

From these first experiences, he learned a critical lesson:

What I learned most from the whole process is there is no way to passively build a successful business. You’re either all in or you’re not. There is no in between.

Tope Awotona

And for his next business, the one that makes him a billionaire, Tope would certainly go all in.

The Aha Moment

The breakthrough for Tope comes while he’s an account manager at EMC:

So I’m selling at EMC and trying to coordinate calendars. All of a sudden, I’m like “this whole experience is awful! I’m trying to schedule with this guy and it’s taking forever.” So I was like, “I’m going to sign up for this app to help me coordinate times.” I tried one and it didn’t satisfy my needs. I tried like 10 others and none of them worked the way I wanted them to. The more I dove in, the more I was unsatisfied.

Tope Awotona

Does he find a clear problem?


Is it one he has personally experienced?


This time, he decides he’s going to do things differently.

Tope described his approach this time around:

I didn’t start off with a position that a business needed to be started. I started off with the position that this problem needed to be researched. I needed to understand the depths of the problem and understand where there was an opening in the market.

Tope Awotona

And research he did.

In an interview with Guy Raz on the How I Built This podcast, Tope would describe how he spent 2-3 months signing up for around 20 or 30 scheduling products to fully understand them.

He’d even engage with their customers on forums to dig up pain points and find an opportunity for a better product.

At the time, it was early 2013, and existing products in the space had poor design. From his research, Tope concludes he can create a better product that serves both sides of the scheduling equation.

He had already learned how to tell the story of a product through demoing the software at Perceptive hundreds of times, had a great deal of sales experience that would come in handy later, and he had learned from a few failed companies.

But he wasn’t committed to making designs just yet.

Trying to Find a Technical Co-Founder

Tope made a detailed list of product requirements and decided he needed to get a technical co-founder. He saw a huge gap in the market through his research and was determined to go after it.

But any founder who has tried to find a technical co-founder knows how much of a struggle it can be.

Hell, Melanie Perkins, the Founder of Canva, took a full year to find her technical co-founder who would eventually help her build their $26B design empire.

So what did Tope do?

He started with his network, reaching out to a talented former co-worker of his.

It didn’t work out.

Finding a technical co-founder was a struggle and here’s how Tope described the experience:

Well I couldn’t find a technical co-founder because all of the best engineers are making a lot of money, and from my experience, most of them have a lower tolerance for risk than business people do and the ones that don’t have a low tolerance for risk, just feel like they can build it themselves and they don’t need to share ownership with someone else. Also, I think a lot of people approach them. I think that is why it’s difficult.

Tope Awotona

Tope talked to dev shops in his city, but they were just motivated by money - he wanted a true partner.

So he did what any of us would probably do.

He turned to Google.

Searching for Ruby dev shops online, he finally found one in Ukraine, Railsware, that was promising, and ended up flying to Ukraine to meet them:

Every time I got on the phone with them, I learned a bit more about the process. They were excited about the work and very knowledgeable. Eventually, I flew to Kiev to meet them. We had an intense 2-day planning session where we scoped out the entire project. It was intense because we had to make a lot of decisions about which calendars do we integrate with and when and much more.

Tope Awotona

But Tope actually came back to the United States thinking he wouldn’t do the idea because he thought it was too big.

Mind you, he’s still working full-time during all of this.

What pushes Tope to finally go after it?

Finding out his mom had terminal cancer.

Tope would have the realization that life is too short to not go after this idea of his.

And remember how I mentioned he went all in?

He emptied his 401k, maxed out his credit cards, got a loan, and poured all of his savings into the $200k development costs of the first version of Calendly.

And the surprising part?

He wasn’t even nervous about it.

He knew about sales, had experience from starting multiple businesses previously, and had thoroughly researched the space for months.

It was go time.

In early 2013, development for Calendly kicks off, taking around 6 months to build, and launching in September 2013.

Then, in November 2013, Tope moves his HQ to the Atlanta Tech Village in an important piece of this story which will come up later.

Unfortunately, during this time, Tope’s mom would die of cancer, never really knowing the full extent of what Tope was building.

Calendly would, however, quickly get its first customers, though as you’re about to learn, they couldn’t make any money from them.

The First Calendly Customers

Calendly in 2013.

Thanks to Web Archive, we can see the original Calendly home page above from 2013.

The first users actually came from Railsware, the dev shop that created it.

Railsware showed Calendly to one of their customers, Bright Bytes, a company in the education space working with K-12 parents, and these parents eventually started using the product for parent-teacher conferences.

With Tope’s focus on building a simple product early on and the viral nature of the product itself, more schools took notice and started using the product for scheduling parent-teacher conferences as well.

At the time, Tope’s plan for monetization was to offer a 14-day free trial to get premium features, with users paying to upgrade. Just one problem - he didn’t have the money to pay for the 2 months of dev work needed to build out the billing functionality.

Of course, Tope eventually needed Calendly to make money.

This is where Atlanta Tech Village, the 100,000-square-foot coworking space Tope joined, comes into the picture.

Calendly’s Initial Funding

It’s early 2014, users are growing fast, and people love the product.

After Tope decides not to go to an accelerator to get funding, he serendipitously meets David Cummings, founder of Atlanta Ventures and Atlanta Tech Village, who previously sold companies for tens of millions of dollars:

I felt like I had come so far with my own money that I didn’t want to get diluted. I felt like I had come so far, put so much into it, and done so much of the hard work. So I filled out the application, I did not complete it. I was just on the fence.

But, someone in the building was using Calendly and tweeted about it. David saw the tweet and we connected after that.

After getting connected, we had many meetings afterwards and I enjoyed meeting him and learning from his insights. I also felt like his brand was good for Calendly and I also felt like I could learn a lot from him and I would enjoy working with him as well.

Tope Awotona

This investment was worth it.

Tope raises $350k of funding, which gives him 9 months of runway and allows him to build in the billing functionality.

He also doesn’t think he would’ve gotten Calendly where it is today without that funding:

I think the business would have grown. I think it would be a profitable business and still be in existence today, there’s no doubt about that. I do think having someone who has a positive way to apply accountability is key and there’s a perspective aspect. There are times in which entrepreneurs are thinking too small and there are times when entrepreneurs are trying to take on too much and there are times when you’re not looking around the corner at what’s next. I think there are times in which you need to recruit people, and you’re in this tiny business and no one knows who you are, it’s helpful for other people to see that successful people believe in you and the future of the business.

Tope Awotona

By August 2014, Tope turns on billing, charging $10 per month or $96 per year.

At the time, they were monetizing a few things: removing the Calendly branding, automated reminders, and personalized notifications.

They end up reaching 15k users in their first full year and around $100k ARR.

In early 2015 Tope raises another $200k but doesn’t end up needing it as they’re growing their revenue so fast, which is what we’ll get to next.

But before we do, I have to mention how Tope differs from many founders in how he goes about funding Calendly.

After raising a total of $550k, he doesn’t raise any more venture capital for nearly 7 years, before making a big splash in 2021.

As Tope mentioned, he didn’t want to get diluted, and indeed he owns a much larger percentage of his company today.

Let’s not get too far ahead of ourselves though, there’s still more to this story.

Calendly Takes Off

We’re going to a bit faster through this next section for two reasons.

  1. Tope’s story of founding Calendly and getting to this point is so crazy I had to cover all of it

  2. I don’t want to just repeat how Calendly keeps growing, but that’s exactly what they do

Fueled by early users who love the product, its viral nature, and Tope’s desire for growth, Calendly takes off.

In 2015, they continue to add features to the premium subscription and start to offer discounts to teams of 5+ people as more companies begin using the product.

According to this article, those changes helped Calendly become profitable and hit $1 million ARR (Annual Recurring Revenue).

2016 brings about more growth as they bring on board enterprise clients, implement a low-touch sales model, and continually build out features to automate the product.

They also build out integrations, grow their inbound sales team, and allow purchase orders as a payment method.

The team is now around 25 employees and they’re doing about $4 million ARR.

By the end of 2017, Tope has grown the team to around 50 employees and they’ve implemented another tier of pricing, their “Pro” plan, and they’re doing about $10 million ARR.

From 2018-2020 they grow from $10 million to about $60 million ARR and by the end of that time have 5 million active users.

That’s when the big news hits.

A $3B Company and Beyond

In January 2021, Calendly announces a $350 million funding round from OpenView Venture Partners and Iconiq Capital valuing them at $3 billion.

But why?

Why raise funding now after being profitable for years and raising so little?

According to this article, the round helped Calendly’s employees and early investors to get some liquidity, while also helping Calendly hire some new executives.

That year, according to Forbes, they did more than $100 million in revenue and had more than 400 employees at the company.

And today?

Tope has a net worth of around $1.2 billion, with Calendly showing no signs of stopping.

Tope’s Wisdom

On working hard:

Towards the end of college I started to realize, no matter how gifted one is, you can be gifted and get away with a lot of stuff, but if you’re going to be in the elite group of people, you also have to supplement that with crazy work ethic.

Tope Awotona

On impatience:

So going back, I’ve never been a patient person. I was patient during my 4 years at the travel agency, but that was because I was very selective with my next move. Now I had IBM on my resume and I wasn’t going to wait around 10 years to become an AE. I still have lots to accomplish.

On growth:

I’m still impatient about the company’s growth. The best entrepreneurs always feel like things can get better. I don’t feel like I’ve made it. I don’t feel like the company has made it. There is still significant room for advancement and growth. That is what I’m impatient about.

Tope Awotona

On hiring:

So, when you're hiring a new role, what I've learned is just to do it slow, maybe hire one or two, so you have a point of comparison. And then once you figure out what success looks like in the role, and what types of people can be successful in the room, what types of skills can be successful in the role? Like truly prove it out? I think then you can hire fast and hire super fast. But never, you know, for me, I don't, I never want to hire super fast. And once I've proven that I know what it takes for those roles to be successful in our business.

Tope Awotona

Thanks for reading! Let me know on Twitter what you thought about this edition of Just Go Grind. If you found this valuable, please consider subscribing and sharing it with a friend 😊 

And if you enjoyed this profile, take a look at the first two - Sam Altman of OpenAI and Melanie Perkins of Canva.

Join the conversation

or to participate.